KR101563379B1 - 아다팔렌 겔의 제조방법 - Google Patents
아다팔렌 겔의 제조방법 Download PDFInfo
- Publication number
- KR101563379B1 KR101563379B1 KR1020107014206A KR20107014206A KR101563379B1 KR 101563379 B1 KR101563379 B1 KR 101563379B1 KR 1020107014206 A KR1020107014206 A KR 1020107014206A KR 20107014206 A KR20107014206 A KR 20107014206A KR 101563379 B1 KR101563379 B1 KR 101563379B1
- Authority
- KR
- South Korea
- Prior art keywords
- adapalene
- water
- delete delete
- propylene glycol
- process according
- Prior art date
Links
- LZCDAPDGXCYOEH-UHFFFAOYSA-N adapalene Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 LZCDAPDGXCYOEH-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 229960002916 adapalene Drugs 0.000 title claims abstract description 49
- 238000004519 manufacturing process Methods 0.000 title abstract description 11
- 239000000499 gel Substances 0.000 title description 32
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000004094 surface-active agent Substances 0.000 claims abstract description 17
- 239000003349 gelling agent Substances 0.000 claims abstract description 15
- 238000002156 mixing Methods 0.000 claims abstract description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 23
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical group COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 20
- 229920002125 Sokalan® Polymers 0.000 claims description 14
- 229920001983 poloxamer Polymers 0.000 claims description 12
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 claims description 10
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 10
- 229960002216 methylparaben Drugs 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- 229920002507 Poloxamer 124 Polymers 0.000 claims description 8
- 229940093448 poloxamer 124 Drugs 0.000 claims description 8
- 239000003755 preservative agent Substances 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical group C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims description 7
- 229960000502 poloxamer Drugs 0.000 claims description 7
- 230000002335 preservative effect Effects 0.000 claims description 7
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 claims description 6
- 229960001631 carbomer Drugs 0.000 claims description 6
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 claims description 4
- RFIMISVNSAUMBU-UHFFFAOYSA-N 2-(hydroxymethyl)-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical group OCC(CO)(CO)COCC=C RFIMISVNSAUMBU-UHFFFAOYSA-N 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 235000013772 propylene glycol Nutrition 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 42
- 239000000203 mixture Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 12
- 208000002874 Acne Vulgaris Diseases 0.000 description 9
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 9
- 206010000496 acne Diseases 0.000 description 9
- 239000008213 purified water Substances 0.000 description 8
- 229920001400 block copolymer Polymers 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- -1 1-adamantyl Chemical group 0.000 description 5
- 239000002738 chelating agent Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229940049638 carbomer homopolymer type c Drugs 0.000 description 4
- 229940043234 carbomer-940 Drugs 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000007689 inspection Methods 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 229920002509 Poloxamer 182 Polymers 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 229940093426 poloxamer 182 Drugs 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 description 2
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical group OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- LXAHHHIGZXPRKQ-UHFFFAOYSA-N 5-fluoro-2-methylpyridine Chemical compound CC1=CC=C(F)C=N1 LXAHHHIGZXPRKQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 2
- 206010047642 Vitiligo Diseases 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000007942 carboxylates Chemical group 0.000 description 2
- 238000007600 charging Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- PZZHMLOHNYWKIK-UHFFFAOYSA-N eddha Chemical compound C=1C=CC=C(O)C=1C(C(=O)O)NCCNC(C(O)=O)C1=CC=CC=C1O PZZHMLOHNYWKIK-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 229960003330 pentetic acid Drugs 0.000 description 2
- 229960005323 phenoxyethanol Drugs 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000009517 secondary packaging Methods 0.000 description 2
- 208000017520 skin disease Diseases 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- 229940043268 2,2,4,4,6,8,8-heptamethylnonane Drugs 0.000 description 1
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- UOVLPWGDOWXYSS-UHFFFAOYSA-N 2-(4-methylphenyl)ethaneperoxoic acid Chemical compound CC1=CC=C(CC(=O)OO)C=C1 UOVLPWGDOWXYSS-UHFFFAOYSA-N 0.000 description 1
- DWHIUNMOTRUVPG-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCO DWHIUNMOTRUVPG-UHFFFAOYSA-N 0.000 description 1
- SGRCVQDBWHCTIS-UHFFFAOYSA-N 2-nonanoyloxypropyl nonanoate Chemical compound CCCCCCCCC(=O)OCC(C)OC(=O)CCCCCCCC SGRCVQDBWHCTIS-UHFFFAOYSA-N 0.000 description 1
- HFAMEIZFPOLNOS-UHFFFAOYSA-N 3-(carboxymethyl)-4-hydroxybenzoic acid Chemical compound OC(=O)CC1=CC(C(O)=O)=CC=C1O HFAMEIZFPOLNOS-UHFFFAOYSA-N 0.000 description 1
- 206010000503 Acne cystic Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
- 208000002506 Darier Disease Diseases 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010023369 Keratosis follicular Diseases 0.000 description 1
- 206010066295 Keratosis pilaris Diseases 0.000 description 1
- 229920003091 Methocel™ Polymers 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- RAPOYLAEZCJMHG-UHFFFAOYSA-N N(2)-{3-[2-(2-{[(1-{3-[2-(2-{[4-(indol-3-yl)butanoyl]amino}ethoxy)ethoxy]propanoyl}piperidin-4-yl)carbonyl]amino}ethoxy)ethoxy]propanoyl}-N(6)-(5-nitro-2-furoyl)lysinamide Chemical compound C1CN(C(=O)CCOCCOCCNC(=O)CCCC=2C3=CC=CC=C3NC=2)CCC1C(=O)NCCOCCOCCC(=O)NC(C(=O)N)CCCCNC(=O)C1=CC=C([N+]([O-])=O)O1 RAPOYLAEZCJMHG-UHFFFAOYSA-N 0.000 description 1
- 206010033554 Palmoplantar keratoderma Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- IRYSNLPWOIOTED-UHFFFAOYSA-N acetic acid ethane-1,2-diamine Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.NCCN.NCCN IRYSNLPWOIOTED-UHFFFAOYSA-N 0.000 description 1
- 208000009621 actinic keratosis Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 229960003168 bronopol Drugs 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229940045110 chitosan Drugs 0.000 description 1
- 229960003260 chlorhexidine Drugs 0.000 description 1
- 229960002242 chlorocresol Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- SOROIESOUPGGFO-UHFFFAOYSA-N diazolidinylurea Chemical compound OCNC(=O)N(CO)C1N(CO)C(=O)N(CO)C1=O SOROIESOUPGGFO-UHFFFAOYSA-N 0.000 description 1
- 229960001083 diazolidinylurea Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229920003111 hydroxyethyl cellulose HHX Polymers 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- KUVMKLCGXIYSNH-UHFFFAOYSA-N isopentadecane Natural products CCCCCCCCCCCCC(C)C KUVMKLCGXIYSNH-UHFFFAOYSA-N 0.000 description 1
- 201000004607 keratosis follicularis Diseases 0.000 description 1
- 229940031674 laureth-7 Drugs 0.000 description 1
- ZADYMNAVLSWLEQ-UHFFFAOYSA-N magnesium;oxygen(2-);silicon(4+) Chemical group [O-2].[O-2].[O-2].[Mg+2].[Si+4] ZADYMNAVLSWLEQ-UHFFFAOYSA-N 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000007908 nanoemulsion Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 201000008743 palmoplantar keratosis Diseases 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 150000004492 retinoid derivatives Chemical class 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US99661807P | 2007-11-27 | 2007-11-27 | |
EP07121665A EP2065032A1 (en) | 2007-11-27 | 2007-11-27 | A method for producing adapalene gels |
EP07121665.9 | 2007-11-27 | ||
US60/996,618 | 2007-11-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20100098539A KR20100098539A (ko) | 2010-09-07 |
KR101563379B1 true KR101563379B1 (ko) | 2015-10-26 |
Family
ID=39247232
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020107014206A KR101563379B1 (ko) | 2007-11-27 | 2008-11-27 | 아다팔렌 겔의 제조방법 |
Country Status (13)
Country | Link |
---|---|
US (1) | US8404220B2 (pt) |
EP (3) | EP2065032A1 (pt) |
JP (2) | JP5526035B2 (pt) |
KR (1) | KR101563379B1 (pt) |
CN (2) | CN101878022B (pt) |
AR (1) | AR071737A1 (pt) |
AU (1) | AU2008328764B2 (pt) |
BR (1) | BRPI0819026B8 (pt) |
CA (1) | CA2706379A1 (pt) |
ES (2) | ES2464455T3 (pt) |
MX (1) | MX2010005432A (pt) |
RU (1) | RU2476203C2 (pt) |
WO (1) | WO2009068610A1 (pt) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK1684782T3 (en) | 2003-10-03 | 2015-11-02 | Thorn Bioscience Llc | PROCEDURE FOR SYNCHRONIZING OVULATION FOR TEMPORARY REGULATED BREEDING WITHOUT BROWN DETECTION |
FR2910320B1 (fr) | 2006-12-21 | 2009-02-13 | Galderma Res & Dev S N C Snc | Emulsion comprenant au moins un retinoide et du peroxyde de benzole |
FR2910321B1 (fr) | 2006-12-21 | 2009-07-10 | Galderma Res & Dev S N C Snc | Gel creme comprenant au moins un retinoide et du peroxyde de benzole |
ES2661240T3 (es) | 2009-04-23 | 2018-03-28 | Jbs United Animal Health Ii Llc | Método y composición para sincronizar el momento de inseminación |
FR2969492B1 (fr) * | 2010-12-23 | 2013-07-05 | Galderma Res & Dev | Mousses dermatologiques obtenues a partir d'un gel ou d'une suspension contenant de l'adapalene |
CN102274159A (zh) * | 2011-07-12 | 2011-12-14 | 广东东阳光药业有限公司 | 一种经皮渗透给药的维甲酸类药物组合物及其制备方法 |
FR2991177B1 (fr) | 2012-06-01 | 2014-12-19 | Galderma Res & Dev | Compositions topiques, contenant un retinoide, de type emulsion huile dans eau sans emulsionnant |
CN103099775B (zh) * | 2012-10-08 | 2014-12-31 | 天津金耀集团有限公司 | 阿达帕林凝胶 |
KR20150095715A (ko) | 2012-11-28 | 2015-08-21 | 제이비에스 유나이티드 애니멀 헬스투 엘엘씨 | 미경산돈에서 수정 시간을 동기화하기 위한 방법 |
TW201625218A (zh) * | 2014-04-18 | 2016-07-16 | Jbs聯合動物保健有限責任公司 | 製造含gnrh凝膠之方法 |
CN105411999A (zh) * | 2015-11-23 | 2016-03-23 | 安徽新和成皖南药业有限公司 | 一种阿达帕林凝胶的制备方法 |
US9987239B1 (en) | 2017-03-14 | 2018-06-05 | Rey Ventures, LLC | Pharmaceutical retinoid preparation for topical use |
CN111759798A (zh) * | 2017-12-21 | 2020-10-13 | 兆科(广州)眼科药物有限公司 | 一种凝胶制剂中阿达帕林的分散工艺 |
WO2019240290A1 (ja) * | 2018-06-16 | 2019-12-19 | ロート製薬株式会社 | 外用組成物 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030170196A1 (en) | 2001-12-21 | 2003-09-11 | Sandrine Orsoni | Dermatological/cosmetic gels comprising at least one retinoid and benzoyl peroxide |
WO2006048747A1 (en) | 2004-11-08 | 2006-05-11 | Glenmark Pharmaceuticals Limited | Topical pharmaceutical compositions containing an antiacne compound and antibiotic compound |
WO2007031883A2 (en) * | 2005-09-16 | 2007-03-22 | Galderma Research & Development | Composition comprising at least one naphthoic acid derivative and at least one compound of polyurethane polymer type or derivatives thereof, preparation processes therefor and uses thereof |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
LU85849A1 (fr) | 1985-04-11 | 1986-11-05 | Cird | Derives benzonaphtaleniques,leur procede de preparation et leur application dans les domaines pharmaceutiques et cosmetiques |
FR2636061B1 (fr) | 1988-09-07 | 1990-11-09 | Cird | Procede de preparation de derives de l'adamantane-1 |
FR2833841B1 (fr) * | 2001-12-21 | 2005-07-22 | Galderma Res & Dev | Gel comprenant au moins un retinoide et du peroxyde de benzoyle |
WO2003075908A1 (en) * | 2002-03-12 | 2003-09-18 | Galderma Research & Development, S.N.C. | Use of adapalene for the treatment of dermatological disorders |
EP1572176A2 (en) * | 2002-12-12 | 2005-09-14 | Galderma Research & Development, S.N.C. | Aqueous-alcoholic depigmenting gel containing a phenolic derivative and a retinoid |
FR2871377B1 (fr) * | 2004-06-11 | 2007-08-24 | Galderma Res & Dev | Gel depigmentant hydroalcoolique comprenant du mequinol et de l'adapalene |
US20080175810A1 (en) * | 2007-01-22 | 2008-07-24 | Jerry Zhang | Topical compositions for cosmetic and pharmaceutical use |
-
2007
- 2007-11-27 EP EP07121665A patent/EP2065032A1/en not_active Withdrawn
-
2008
- 2008-11-27 MX MX2010005432A patent/MX2010005432A/es active IP Right Grant
- 2008-11-27 EP EP08855104.9A patent/EP2224906B1/en active Active
- 2008-11-27 BR BRPI0819026A patent/BRPI0819026B8/pt not_active IP Right Cessation
- 2008-11-27 CN CN200880117947.3A patent/CN101878022B/zh not_active Expired - Fee Related
- 2008-11-27 WO PCT/EP2008/066339 patent/WO2009068610A1/en active Application Filing
- 2008-11-27 AR ARP080105151A patent/AR071737A1/es active IP Right Grant
- 2008-11-27 EP EP12156072.6A patent/EP2460513B1/en active Active
- 2008-11-27 JP JP2010535378A patent/JP5526035B2/ja not_active Expired - Fee Related
- 2008-11-27 ES ES08855104.9T patent/ES2464455T3/es active Active
- 2008-11-27 CA CA2706379A patent/CA2706379A1/en not_active Abandoned
- 2008-11-27 CN CN201410009946.4A patent/CN103830163B/zh not_active Expired - Fee Related
- 2008-11-27 RU RU2010126103/15A patent/RU2476203C2/ru active
- 2008-11-27 ES ES12156072T patent/ES2887225T3/es active Active
- 2008-11-27 AU AU2008328764A patent/AU2008328764B2/en not_active Ceased
- 2008-11-27 KR KR1020107014206A patent/KR101563379B1/ko active IP Right Grant
-
2010
- 2010-05-25 US US12/786,885 patent/US8404220B2/en active Active
-
2014
- 2014-02-06 JP JP2014021388A patent/JP2014101373A/ja active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030170196A1 (en) | 2001-12-21 | 2003-09-11 | Sandrine Orsoni | Dermatological/cosmetic gels comprising at least one retinoid and benzoyl peroxide |
WO2006048747A1 (en) | 2004-11-08 | 2006-05-11 | Glenmark Pharmaceuticals Limited | Topical pharmaceutical compositions containing an antiacne compound and antibiotic compound |
WO2007031883A2 (en) * | 2005-09-16 | 2007-03-22 | Galderma Research & Development | Composition comprising at least one naphthoic acid derivative and at least one compound of polyurethane polymer type or derivatives thereof, preparation processes therefor and uses thereof |
Also Published As
Publication number | Publication date |
---|---|
JP2014101373A (ja) | 2014-06-05 |
MX2010005432A (es) | 2010-06-02 |
BRPI0819026B1 (pt) | 2020-05-05 |
JP2011504912A (ja) | 2011-02-17 |
AU2008328764A1 (en) | 2009-06-04 |
ES2464455T3 (es) | 2014-06-02 |
US8404220B2 (en) | 2013-03-26 |
EP2460513B1 (en) | 2021-07-21 |
KR20100098539A (ko) | 2010-09-07 |
RU2476203C2 (ru) | 2013-02-27 |
CN103830163A (zh) | 2014-06-04 |
BRPI0819026B8 (pt) | 2021-05-25 |
AR071737A1 (es) | 2010-07-14 |
US20100280121A1 (en) | 2010-11-04 |
ES2887225T3 (es) | 2021-12-22 |
EP2460513A1 (en) | 2012-06-06 |
EP2224906A1 (en) | 2010-09-08 |
CN103830163B (zh) | 2016-12-07 |
AU2008328764B2 (en) | 2013-11-21 |
CA2706379A1 (en) | 2009-06-04 |
EP2224906B1 (en) | 2014-02-19 |
BRPI0819026A2 (pt) | 2017-04-04 |
CN101878022A (zh) | 2010-11-03 |
JP5526035B2 (ja) | 2014-06-18 |
EP2065032A1 (en) | 2009-06-03 |
CN101878022B (zh) | 2014-02-19 |
WO2009068610A1 (en) | 2009-06-04 |
RU2010126103A (ru) | 2012-01-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR101563379B1 (ko) | 아다팔렌 겔의 제조방법 | |
JP4579411B2 (ja) | 全身作用を有する局所ホルモン組成物 | |
DK2450035T3 (en) | Combination of adapalene and benzoyl peroxide for the treatment of acne lesions | |
JP5989095B2 (ja) | イブプロフェンの経皮組成物およびその使用方法 | |
US20150216834A1 (en) | Pharmaceutical/cosmetic, e.g., anti-acne compositions comprising at least one naphtoic acid compound, benzoyl peroxide and at least one film-forming agent | |
EP2817069A1 (en) | Composition comprising a retinoid and benzoyl peroxide | |
US20100004338A1 (en) | Topical gel composition comprising azelaic acid | |
WO2007071861A2 (fr) | Compositions comprenant au moins un compose retinoide et au moins un compose anti-irritant et leurs utilisations | |
US20200338023A1 (en) | Non-toxic topical formulations of dapsone | |
US8937098B2 (en) | Dermatological compositions comprising at least one naphthoic acid compound and at least one film-forming agent and treatment of keratinization disorders therewith | |
EP1965786A2 (fr) | Compositions comprenant au moins un compose retinoide et au moins un compose anti-irritant et leurs utilisations | |
WO2021061913A1 (en) | Diclofenac sodium topical solution | |
WO2002004012A1 (en) | Anhydrous pharmaceutical composition of vancomycin for topical use | |
JP6925275B2 (ja) | 皮膚用の医薬組成物 | |
WO2011135073A1 (de) | Adhesive retardformulierungen zur lokalen verabreichung von curcumin | |
JP7214331B2 (ja) | 医薬組成物 | |
JP2023001391A (ja) | 医薬組成物 | |
BG2764U1 (bg) | Набор за практическо обучение по химия и опазване на околната среда | |
NZ618259B2 (en) | Transdermal compositions of ibuprofen and methods of use thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
AMND | Amendment | ||
E902 | Notification of reason for refusal | ||
AMND | Amendment | ||
E601 | Decision to refuse application | ||
AMND | Amendment | ||
J201 | Request for trial against refusal decision | ||
B701 | Decision to grant | ||
GRNT | Written decision to grant | ||
FPAY | Annual fee payment |
Payment date: 20180918 Year of fee payment: 4 |
|
FPAY | Annual fee payment |
Payment date: 20190917 Year of fee payment: 5 |